Seeking advice from the pros

[Clay L.]

Hey BP, I'll try to make this brief and explain my situation. I know I need to make a move but have been frozen for a year trying to decide. Here goes.

I'm a 33 year old guy, single, live in Aurora Colorado (just across the Denver line). I'm a consultant who travels 50% and works from home 50% so I can live wherever I want. I earn around 140k from this job. I'm 1099 with only 1 year income to show currently. Made similar money at previous W2 job. This could potentially factor into getting loans.

I own a primary residence in Aurora (valued around 300k, owe 150k). The place is very small and I used to house hack and had a roommate but got tired of it because the place is so small, now living alone.

I also own an investment property that I airbnb in the mountains 1 hour away (valued around 340k, owe 240k). The airbnb brings in on average $2,250 per month net income after all expenses and mortgage paid. This property is fairly hands on and requires around 4 hours per week of messaging guests, updating pricing, buying supplies + 1-2 visits per month to deliver supplies and property manage.

I enjoy Colorado but am not bound to it. Again, I can live anywhere. I at least would want to be in a city with a decent airport.

I know there are a million variables regarding my real estate/financial goals, etc, but I'm just looking to see what others would do. I'm curious what creative strategies people would use to maximize their assets in a similar situation.

To recap:

My primary residence is worth $300k, with $150k equity. This home would rent for $1600 per month easy, mortgage is $1,000.

My investment property airbnb is worth $340k with $100k equity. $2250 average cash flow per month. The airbnb is very hands on and requires 1-2 visits per month to keep in good shape, also it's often difficult to find people to help out high up in mountains.

I have considered selling everything and cashing out and moving to another city where I can buy a home in cash (near a decent airport). I then accomplish a goal of owning a home free and clear but I then tie up all my cash in one property. I want to be conservative but probably not that conservative.

I change my mind everyday on what I want to do but maybe some of the brilliant minds here can spark an idea that I will be confident to move forward with! Thanks in advance for sharing your knowledge.